Unlock the Florida Keys: Key West Weekend Travel Guide

Key West, in a nutshell, is tropical paradise. Although it’s only 7 hours driving distance from Central Florida, my girlfriends and I hadn’t been in over 10 years… the last occasion being Lake Highland Sea Camp in 7th grade. This was just the long weekend of relaxation I needed to break up my 75-hour weeks at work, and I can’t say enough how grateful I am to The Gates Hotel Key West for opening their doors to us. Additionally, Mike Freas of Foto by Freas is as fun as he is talented, and Ash and I are so lucky we convinced him to take our pictures during this trip. Keep reading for a comprehensive Key West weekend travel guide, including what to do and where to stay!

The Gates Hotel Key West is a brand new upscale boutique hotel right across from the water. Designed in a modern, minimal style which highlights local architectures, artists, and talent, I was stunned by the simplicity of their contemporary island decor. From the second we received our room keys, all we wanted to do was take a nap and explore the island. A nap won first, though. Also, within the first 5 minutes of the unpacking process, we completely covered all free surface area with bags, jewelry, and accessories.

When I say The Gates gave us a warm welcome, I mean a blazinglysunny, warm welcome. Upon walking into their lobby, I was handed a personalized birthday card, complete with signatures and messages from each and every member of their team. Needless to say, I felt like a certified VIP from the very beginning.

In addition to their exemplary kindness, The Gates has an amazing pool with white recliners and cabanas lined symmetrically on both sides, as well as blue and pink noodles floating for relaxation at your convenience, features a hopping poolside bar and lounge area called Rum Row for enjoying as many daiquiris as your heart can handle, and even hosts a stationary food truck called The Blind Pig.

I know you’re thinking, “Seriously? A food truck?!,” but it makes so much sense for a resort dedicated to promoting local talent. Named after a slang term for speakeasy, The Blind Pig is a nod to Key West’s role in Prohibition and dishes out a selection of “Conch fusion” small bites and tapas, a style of cuisine inspired by Key West’s Cuban, Bahamian, Caribbean, and Floridian roots.

Did I mention I was blessed with the presence of two of my ultimate BFFs, Ashley Brooke and Christy Alexa? Christina refused to be photographed 98% of the time, though. I promise she still claims she had fun. Thanks again, Foto by Freas, for the awesome photography, and you can find my outfit details here!

After a brief business breakfast meeting, it was time to get ready for a shopping spree at Lilly Pulizer Key West and, of course, take a highly anticipated tour of the Key West’s First Legal Rum Distillery. Playing off Key West’s history as a port for liquor smuggling during prohibition, this authentic and only-in-Key-West operation distills and crafts its own specialty rums.

Side note: First Legal’s Key West-distilled rum is available at The Gates Key West and is featured as a custom rum on the menu of Rum Row. Pretty cool.

And then there was Lilly. A full recap post is to come, but my-oh-my, hanging out in Lilly Pulitzer‘s first corporate store and learning all about its history of pattern making and print design was fascinating.

We may also have been dangerously close to stealing all of their furniture. PS- I apologize about the iPhone quality photo(s).

My wallet walked away from Lilly Pulitzer Key West moderately unscathed- with a mere two bags in tow- and continued my way into what looks like a botanical jungle. You can find all my outfit details here.

Upon the gracious recommendation of Lilly Pulitzer Key West’s manager, Rocco, we stopped for lunch down the street at The Pierhouse’s Harbourview Cafe. Emphasis on the VIEW part. The food was delicious, and the crystal clear blue water was breathtaking.

After lunch, we stopped by the pool for a bit, napped by the pool for a bit, and got ready for a highly anticipated dinner at Hot Tin Roof Key West. It’s literally tucked away in the luscious greenery of the Keys, and its casual elegance is known to provide the absolute best waterfront dining overlooking Key West Harbor.

Oh, and their mango mojitos were incredible.

Unfortunately for us Central Floridians, the super late southern sunsets, thanks to DST, are 1000% more dazzling in Key West.

For brunch the next day, we headed back downtown for cocktails at La Te Da, aka the most sophisticatedly eccentric hotel restaurant in all of Key West. Yep, that’s a Burlesque show poster in the background– and yep, it’s hosted at the hotel.

Also, I’ve you’ve never had one of their Strawberry Lemon Basis mimosas, you haven’t lived life to your fullest potential.

Proof that taking a photo of three women is never as easy at it seems.

We spent the rest of the day shopping, sight-seeing, and hanging out at the hotel. We also made an obligatory stop by Kermit’s for some of their famous key lime pie!

Later that night, we were invited by our new friend and photographer Mike Freas to experience a real Key West sunset on our own private sunset boat tour. Sunset Sail Key West was hands down the most fabulous way to spend our last evening on the island.

Our privately-chartered classic sailboat, which was operated by the way-cooler-than-me Captain and Mate, took us out into the harbor, hoisted the sails, and turned off the engine– leaving us with complete peace, tranquility, and quality time. It was wonderful. Their private sailboats actually hold up to 6 guests, so I highly recommend checking out Sunset Sail Key West if you’re looking for a unique | peaceful | romantic | platonic | team-building activity in the Keys.

I’d been eyeing them all weekend, but my laziness kept reigning victorious– so on our last morning at The Gates, we had to take their Lorenzo Martone Bicycles for a spin around Old Town Key West. Their bike rentals are available by hour or by day, which is nice, and are available to anyone and everyone staying at the hotel. We even saw a few iguanas climbing up palm trees. Nature.

After a rousing 30-minute (or less) bike ride, we needed to replenish our strength with some brunch at The Blind Pig, which we enjoyed poolside– primarily for cooling down purposes.

After brunch it was time to pack up our ridiculous arsenal of belongings and head back to Orlando. I seriously considered going on the lamb and disappearing in the islands, but my wealth management firm needs me too much for that. Dang it.

This was such a rare and special girls weekend for me and my BFFs, and I can’t wait to go back. With everything going on in life, sometimes it’s hard to stop and remember to celebrate the ones you love most– even if it means requesting a few days off your busy work schedule, finding a nanny (ohhh how depressing it is to say that), or spending a little extra money.

Thank you again, The Gates Hotel Key West, for your warm hospitality and unique sensation of what my brother calls “the cool island breeze.”You’re the best! Also, if you’ve been to the Florida Keys yourself, what else would you add to my Key West weekend travel guide?